87106-27-2

Upstream product

• 16958-25-1 (R)-3-methylpentanoic acid 
• 3112-85-4 methylphenylsulfonate 
• 61530-30-1 (R)-sec-butyl 4-methylbenzenesulfonate 
• 94807-84-8 (S)-3-Methyl-4-phenylsulfanyl-butyric acid ethyl ester 
• 94807-95-1 Methanesulfonic acid (S)-3-methyl-4-phenylsulfanyl-butyl ester 
• 94807-93-9 (S)-3-methyl-4-phenylthio-1-butanol 
• 78505-05-2 (3S)-3-methyl-4-phenylsulfonylbutanol 
• 94807-80-4 Methanesulfonic acid (S)-4-benzenesulfonyl-3-methyl-butyl ester 
• 82363-37-9 ((S)-2-Methyl-butylsulfanyl)-benzene 
• 50896-54-3 (S)-(+)-1-methylpropyl p-toluenesulfonate 
• 87144-80-7 methyl (R)-(+)-7-hydroxy-3,7-dimethyl-5-octenoate 
• 79936-62-2 methyl (3R)-3-methyl-5-oxopentanoate 
• 87106-25-0 (R)-(+)-1-iodo-2-methylbutane 
• 3406-02-8 bis(phenylsulfonyl)methane 

Downstream Products

• 87106-30-7 (3R,7R)-3,7-dimethylnonyl tosylate 
• 71777-34-9 (R)-(-)-10-methyl-1-dodecanol acetate 
• 87106-28-3 (3R,7R)-3,7-dimethyl-6-benzenesulfonylnonyl benzyl ether 
• 91787-38-1 2-methyl-1-phenylsulphonyl-1-trimethylsilylbutane 

Relevant academic research and scientific papers

Synthesis of four stereoisomers of (S)-2-methylpent-3-yl 3,13-dimethylpentadecanoate, a sex pheromone of the bagworm moth clania variegate, using stereospecific inversion of secondary sulfonates as a key step

Females of some lepidopteran species produce novel sex pheromones with a methyl-branched structure, such as 2-methylpent-3-yl 3,13-dimethylpentadecanoate secreted by the bagworm moth Clania variegate. Recently, we have established a simple preparative method for the synthesis of methyl-branched building blocks by utilizing an SN2 reaction of chiral secondary tosylates derived from (S)- and (R)-propylene oxides. The usefulness of these building blocks was demonstrated by their application in the synthesis of all four stereoisomers of an acid moiety in the bagworm pheromone. The enantiomeric purities of all building blocks were confirmed by enantioselective HPLC analysis. We found that a secondary mesylate was superior to the corresponding tosylate because it avoided an elimination side reaction, and racemization in the SN2 reaction was not observed even at high temperature (150 °C). Finally, each optically active acid was esterified with (S)-2-methyl-3-pentanol, which was synthesized by a new route starting from (S)-valine. A simple route to methyl-branched building blocks has been developed by utilizing an S N2 reaction of chiral secondary sulfonates derived from (S)- and (R)-propylene oxides. The usefulness of these building blocks was demonstrated by the stereospecific synthesis of all four stereoisomers of a bagworm pheromone. Copyright

Stereospecific Dehydrative Alkylation of Bis-Sulfones: Synthesis of a Lesser Tea Tortrix Pheromone

The intra- and intermolecular condensation of alcohols with bis-sulfone methylenes, i.e., dehydrative alkylation, using DEAD and Ph3P proceeds stereospecifically at room temperature under essentially neutral conditions affording good to excellent yields o

SYNTHESIS OF ALL OF THE FOUR POSSIBLE STEREOISOMERS OF 4,8-DIMETHYLDECANAL, THE AGGREGATION PHEROMONE OF THE FLOUR BEETLES

The four stereoisomers of 4,8-dimethyldecanal were synthesized employing organometallic or electrolytic coupling reactions as the key step.The response of the red flour beetle, Tribolium castaneum, to the (4R,8R)-isomer was identical with that to the natural pheromone, while other isomers induced only very weak or no responses.The (4R,8R)-isomer is therefore the natural pheromone.